Many discourses link media with generations, ascribing particular appetence for the use of new media to youth, in contrast with older generations. This article aims to give an account of the empirical regularities but also differences found in a longitudinal quantitative analysis of Internet users, uses, and media preferences among different Portuguese age cohorts. Making use of questionnaire surveys with representative samples, the importance of generational belongings in structuring different types of relationships with media is demonstrated, as youngsters seem to prefer new media. However, this variable does not hold in itself complete explanatory power. The importance of formal education, besides other sociographic variables, is clear, indicating the existence of social disparities within age cohorts, with repercussions on the mediated access to resources and opportunities. The diversity and inequalities found through the statistical analysis help to combat the rhetoric of a supposedly innate, all-encompassing digital nativity. By adopting a social constructivist approach, with a more holistic scope, this article also aims to reconstruct part of the complexity and multidimensionality of the relationship between and within Portuguese generations with media, thereby deconstructing more essentialist and homogenising notions of youth and generations.